Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One‐pot Synthesis of Benzoxazoles

Moghaddam, Firouz Matloubi; Saberi, Vahid; Kalhor, Sepideh; Veisi, Nazila

doi:10.1002/aoc.4240

Cited by 20 publications

(18 citation statements)

References 62 publications

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“…Among the methods utilized for the formation of benzoxazole rings, the synthesis of a 2‐substituted derivative from 2‐aminophenol as starting material stands out. Many studies in the literature point out to obtain a high yield benzoxazole ring (Scheme 1A) [15–27] . In addition to the necessity in improving the reaction conditions, it is also essential to place the carbonyl group in the C‐2 position of the oxazole ring instead of the aryl ring substitution, which will not allow much further derivatizations easily.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzoxazole‐2‐carboxylate Derivatives: Electronic‐ and Position‐effect of Functional Groups and Computational Modeling of the Selectivity for Oxazole Ring

et al. 2021

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In this study, Mitsunobu reagent, DEAD (diethyl azodicarboxylate) and PPh3, and ethyl‐oxalamide derivatives of 2‐aminophenol were reacted under mild reaction conditions. As a result of the cyclization reaction, benzoxazole derivatives bearing an ester group in the C‐2 position were obtained in a one‐pot protocol. It was observed that the electron‐donating groups at the C‐5 position and the electron‐withdrawing groups at the C‐6 position of the benzene ring increased the yield of the cyclic product. It was found that the cyclization does not occur when the carboxylic acid group is substituted in the benzene ring. The cyclization reaction we performed preferred the 5‐endo‐trig reaction instead of the 6‐exo‐trig. This experimental result was examined in detail with density functional theory (DFT) calculations as well. A computational exploration is presented herein that elucidates the detailed mechanism for Huisgen zwitterion‘s reaction with ethyl‐oxalamide derivatives of 2‐aminophenol. Potential alternative mechanisms were modeled with DFT calculations via CPCM/M06‐2X/6‐311++G(d,p)//B3LYP/6‐31+G(d,p) level method in tetrahydrofuran to understand shed light on the mechanism. Our computational results are in good agreement with experimental findings that benzoxazole derivatives are the sole products in this reaction.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Benzoxazole‐2‐carboxylate Derivatives: Electronic‐ and Position‐effect of Functional Groups and Computational Modeling of the Selectivity for Oxazole Ring

et al. 2021

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“…The magnetic nanoparticle (Fe 3 O 4 ) was synthesized using the co-precipitation approach 101 , 102 . After synthesizing it, Fe 3 O 4 @SiO 2 (1 g) was dispersed in dry EtOH and NH 4 OH (2 mL) was added to the mixture.…”

Section: Methodsmentioning

confidence: 99%

Magnetic UiO-66 functionalized with 4,4′-diamino-2,2′-stilbenedisulfonic as a highly recoverable acid catalyst for the synthesis of 4H-chromenes in green solvent

Khodabakhshi

Baghersad

2022

Sci Rep

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According to 4H-chromenes importance, we synthesized a novel magnetic UiO-66 functionalized with 4,4′-diamino-2,2′-stilbenedisulfonic as an efficient and reusable solid acid catalyst for synthesizing 4H-chromene skeletons via a one-pot three components reaction in a green solvent. The structure of the synthesized catalyst was confirmed by various techniques including FT-IR, XRD, BET, TGA, TEM, EDX, and SEM, and also the product yields were obtained in 83–96% of yields for all the reactions and under mild conditions. The reported procedure presents an environmentally friendly approach for synthesizing a significant number of 4H-chromene derivatives. Correspondingly, MOF-based catalyst makes it easy to separate from reaction media and reuse in the next runs.

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“…[ 18 ] Most of the reported procedures have used copper [ 18d,e ] or other catalysts. Palladium‐catalysed synthesis of benzoxazoles from aldehydes and o ‐aminophenol was reported by Moghaddam et al [ 19 ] But the reaction took a long time (18 h) for completion. In palladium‐catalysed reactions, generally palladium exist as Pd(0) and Pd(II), [ 20 ] although the utility of Pd (IV) [ 21 ] has been steadily emerging in its own right.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous palladium (II)‐complexed dendronized polymer: A rare palladium catalyst for the one‐pot synthesis of 2‐arylbenzoxazoles

George

Sreekumar

2020

Applied Organom Chemis

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The palladium complex of dendronized amine polymer (EG-Gn-Pd, n = 0, 1 and 2) having ethylene glycol-initiated polyepichlorohydrin as core was synthesized on a Merrifield resin support and was well characterized. Generally, palladium catalysts are known for carbon-carbon coupling reactions. Here, a developed catalyst was found to be good for benzoxazole synthesis. Higher generation dendronized polymer (EG-G2-Pd) was found to be better catalyst over lower generation dendronized polymers. Moreover, dendronized polymers were found to be a better catalyst over dendrigraft polymers. The catalyst reusability was checked and good yield was obtained for five cycles.

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Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One‐pot Synthesis of Benzoxazoles

Cited by 20 publications

References 62 publications

Synthesis of Benzoxazole‐2‐carboxylate Derivatives: Electronic‐ and Position‐effect of Functional Groups and Computational Modeling of the Selectivity for Oxazole Ring

Synthesis of Benzoxazole‐2‐carboxylate Derivatives: Electronic‐ and Position‐effect of Functional Groups and Computational Modeling of the Selectivity for Oxazole Ring

Magnetic UiO-66 functionalized with 4,4′-diamino-2,2′-stilbenedisulfonic as a highly recoverable acid catalyst for the synthesis of 4H-chromenes in green solvent

Heterogeneous palladium (II)‐complexed dendronized polymer: A rare palladium catalyst for the one‐pot synthesis of 2‐arylbenzoxazoles

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